Joe Morrell and Abu Kamara missed their spot-kicks as Portsmouth lost 5-4 on penalties to Peterborough after a 1-1 draw in the second round of the Carabao Cup.
Kamara had the chance to send Pompey through after Ryan De Havilland had seen his penalty saved by Ryan Schofield but blazed into the stands.
Wales midfielder Morrell then crashed his effort against a post before David Ajiboye stepped up to win it for 10-man Posh.
Pompey had the first effort after five minutes as a solid strike from Terry Devlin was deflected over for a corner, whilst at the other end Ajiboye tested Schofield from distance.
Posh took the lead after 29 minutes when an in-swinging corner caused problems and Ajiboye bundled the ball home from close range.
It took only six minutes of the second half for Pompey to equalise as a cross from Paddy Lane fell to Christian Saydee who, with his back to goal, swivelled to beat James Dornelly and goalkeeper Fynn Talley.
Peterborough’s Charlie O’Connell saw red after a second yellow card for a foul on Terry Devlin in the 59th minute, having already been booked for kicking the ball away in the first half.
Portsmouth threw everything at Peterborough’s 10 men and substitute Colby Bishop should have won it but failed to convert from point-blank range and it was the visitors who prevailed on penalties.
